Multifunctional 1,3-benzoxazole-merocyanine-based probe for the ratiometric fluorescence detection of pH/HSO3−/viscosity in mitochondria

Wei Na Wu; Yu Fei Song; Xiao Lei Zhao; Yuan Wang; Yun Chang Fan; Zhi Hong Xu; Tony D. James

doi:10.1016/j.cej.2023.142553

Multifunctional 1,3-benzoxazole-merocyanine-based probe for the ratiometric fluorescence detection of pH/HSO₃⁻/viscosity in mitochondria

Wei Na Wu, Yu Fei Song, Xiao Lei Zhao, Yuan Wang, Yun Chang Fan, Zhi Hong Xu, Tony D. James

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

68 Citations (SciVal)

Abstract

pH, HSO₃⁻, and viscosity are crucial bio-markers for evaluating the status of mitochondria in the cell micro-environment. With this research, we developed a ratiometric mitochondria-targeting fluorescent probe 1 that was responsive toward bisulphite, pH and viscosity. Hydroxylphenyl 1,3-benzoxazole (D) acted as a pH recognition unit; benzo[e]indolium (A) acted as a fluorescent rotor to achieve a viscosity response; the C = C bond constructed by bridging D and A was susceptible to nucleophilic attack and hence responded to HSO₃⁻. Probe 1 exhibits significant ratiometric signal changes, high sensitivity, outstanding selectivity, and good stability for detecting pH, viscosity, and SO₂ in solution. Probe 1 was used for imaging pH, viscosity, and SO₂ derivatives in live cells and zebrafish, indicating its potential for identifying mitochondrial dysfunctions.

Original language	English
Article number	142553
Journal	Chemical Engineering Journal
Volume	464
Early online date	22 Mar 2023
DOIs	https://doi.org/10.1016/j.cej.2023.142553
Publication status	Published - 15 May 2023

Bibliographical note

Funding Information:
This work was supported in part by the National Natural Science Foundation of China (No. 21907023 and 21001040), the Joint Program for Fostering Talents of National Natural Science Foundation of China and Henan Province (No. U1304202 and U1604124), the State Scholarship Fund (No. CSC 201908410366), the Science and Technology Department of Henan Province (No. 212102210033, 212102310388, 222102320069, 222300420523 and 212102210646), Key Program of Xuchang University (No. 2019-JC-02), the Scientific Research Innovation Team of Xuchang University (No. 2022CXTD001) and the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University (No. 2020ZD01).

Data availability
All data generated or analysed during this research are included in this published article and as part of the supplementary information.

Keywords

Bioimaging
HSO
pH
Ratiometric fluorescent probe
Viscosity

ASJC Scopus subject areas

General Chemistry
Environmental Chemistry
General Chemical Engineering
Industrial and Manufacturing Engineering

Access to Document

10.1016/j.cej.2023.142553Licence: CC BY

Cite this

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title = "Multifunctional 1,3-benzoxazole-merocyanine-based probe for the ratiometric fluorescence detection of pH/HSO3−/viscosity in mitochondria",

abstract = "pH, HSO3−, and viscosity are crucial bio-markers for evaluating the status of mitochondria in the cell micro-environment. With this research, we developed a ratiometric mitochondria-targeting fluorescent probe 1 that was responsive toward bisulphite, pH and viscosity. Hydroxylphenyl 1,3-benzoxazole (D) acted as a pH recognition unit; benzo[e]indolium (A) acted as a fluorescent rotor to achieve a viscosity response; the C = C bond constructed by bridging D and A was susceptible to nucleophilic attack and hence responded to HSO3−. Probe 1 exhibits significant ratiometric signal changes, high sensitivity, outstanding selectivity, and good stability for detecting pH, viscosity, and SO2 in solution. Probe 1 was used for imaging pH, viscosity, and SO2 derivatives in live cells and zebrafish, indicating its potential for identifying mitochondrial dysfunctions.",

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note = "Funding Information: This work was supported in part by the National Natural Science Foundation of China (No. 21907023 and 21001040), the Joint Program for Fostering Talents of National Natural Science Foundation of China and Henan Province (No. U1304202 and U1604124), the State Scholarship Fund (No. CSC 201908410366), the Science and Technology Department of Henan Province (No. 212102210033, 212102310388, 222102320069, 222300420523 and 212102210646), Key Program of Xuchang University (No. 2019-JC-02), the Scientific Research Innovation Team of Xuchang University (No. 2022CXTD001) and the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University (No. 2020ZD01). Data availability All data generated or analysed during this research are included in this published article and as part of the supplementary information. ",

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AU - Zhao, Xiao Lei

AU - Wang, Yuan

AU - Fan, Yun Chang

AU - Xu, Zhi Hong

AU - James, Tony D.

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N2 - pH, HSO3−, and viscosity are crucial bio-markers for evaluating the status of mitochondria in the cell micro-environment. With this research, we developed a ratiometric mitochondria-targeting fluorescent probe 1 that was responsive toward bisulphite, pH and viscosity. Hydroxylphenyl 1,3-benzoxazole (D) acted as a pH recognition unit; benzo[e]indolium (A) acted as a fluorescent rotor to achieve a viscosity response; the C = C bond constructed by bridging D and A was susceptible to nucleophilic attack and hence responded to HSO3−. Probe 1 exhibits significant ratiometric signal changes, high sensitivity, outstanding selectivity, and good stability for detecting pH, viscosity, and SO2 in solution. Probe 1 was used for imaging pH, viscosity, and SO2 derivatives in live cells and zebrafish, indicating its potential for identifying mitochondrial dysfunctions.

AB - pH, HSO3−, and viscosity are crucial bio-markers for evaluating the status of mitochondria in the cell micro-environment. With this research, we developed a ratiometric mitochondria-targeting fluorescent probe 1 that was responsive toward bisulphite, pH and viscosity. Hydroxylphenyl 1,3-benzoxazole (D) acted as a pH recognition unit; benzo[e]indolium (A) acted as a fluorescent rotor to achieve a viscosity response; the C = C bond constructed by bridging D and A was susceptible to nucleophilic attack and hence responded to HSO3−. Probe 1 exhibits significant ratiometric signal changes, high sensitivity, outstanding selectivity, and good stability for detecting pH, viscosity, and SO2 in solution. Probe 1 was used for imaging pH, viscosity, and SO2 derivatives in live cells and zebrafish, indicating its potential for identifying mitochondrial dysfunctions.

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